How I Style It: First Date Looks

first night

Good morning all! So today we are linking up with Bright on a Budget, Della Devoted, Garay Treasures, bybmg and Glitter + Ruffles in the How I Style It Look. I’m also linking up with Jersey Girl Texan Heart in her Wednesday link-up.

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Jersey Girl, Texan Heart Link Up

So I initially found out about the How I Style It link-up in an email from Tif at Bright on a Budget. I subscribe to bloggers who are where I’d like to be one day, and she is for sure one of them. When I saw that it was about a date night look, it got me thinking. Truth be told, I’m not dating anyone right now. The last time I’ve been on a “date” was about six months ago.

Then I started thinking about the first date and how I would style a first date look if I were to go on one. I’m a fan of The Mindy Project and I remember first season one of the characters telling Mindy that her first date outfit was too much. I can’t remember the character … one of the guys. He said something like “minimal make, simple dress.” It’s funny how that moment has stuck out in my head since.

Furthermore, I’m sure there are lots of ladies out there unsure of what to wear on a first date. It is for sure nerve-wracking. Also since many of us Internet date now, this may be the very first time you’re meeting the person face-to-face. Making a good first impression is key.

So here are my rules guidelines for first date looks:

1. Something classically me

first date

I cannot tell you how many times I’ve worn this dress. You’d think I’d found it at a vintage store, but I actually found it at Target about a year and a half ago. It is comfy and easy to style.

2. Something simple and classy

first date

A first date is not the time to try anything crazy or too fashion-forward. This dress is just a simple piece that zips up the back. Furthermore, it looks great in the summer with a simple pair of flat sandals, black heels or as is in the picture with some boots. I also wear these boots all the time. Also if you’re taller like me, opting for flat shoes can be great. There’s nothing more awkward (at least for me) than being taller than the guy when you meet. I don’t know … I always like the guys I date to be taller than me.

3. Jewelry and Makeup simple

first date

These pictures were taken yesterday at 8 a.m., providing for a lot of sunlight and interesting shadows. The only jewelry I’m wearing are a pair of black earrings I got in Nicaragua. My hair is pulled back. I also often just have my hair long and down. Again simple and nothing too crazy.

first date

first date

Well those are a few of my tips for first date looks. What tips do you have when dressing for a first date? Feel free to leave me comments below about what you’ve found to work. Also funny stories are always welcomed. I have a few of those for sure too.

Also linking up with:


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